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How to make a move

I've been spending time (mostly hiking and other outdoorsy stuff) with someone that I am interested in. I am 99% certain that he is interested too. He is related through marriage to one of my best friends and she has said as much, and most of his actions seem to back that up. However, despite being given several opportunities, he has not made a move. He continues to invite me to do things, and to accept my invitations, but physically, nothing has happened. Best friend (his stepsis) has said he is shy, and I will probably have to make the move.

I've never really had this problem before. I've never chased guys, the ones I ended up dating had no issues making a move. I feel like I should just wait for him to work up the nerve, and that if he is interested he will, but some friends say to just go for it and let him off the hook. Not really sure what constitutes a "move". I feel like whatever I will do will be awkward and obvious, because I'm not practiced at this.

Are there any forward ladies or shy guys out there willing to share what works? Even just a way to let him know I am open to it...since he's sort of awkward, any time he does something I think might be flirting I get completely stupid and end up probably ruining the moment. I've never really been that way, but haven't met someone like him before so I want to respect his boundaries but also let him know I am interested. (this should be easier!)

Honestly, I'm going to say wait for him to do it. Not because guys are required to make the first move, but because it sounds like he might appreciate you waiting until he's ready.

If that method doesn't strike your fancy, well... does he drink? Not that you want to cross any lines, but a little liquid courage always seems to make people a little more friendly.

Barring those two ideas...without knowing where you're currently at (no physical contact at all? no flirting?), just start with the next "step". If you're not currently making any physical contact at all, you can always take his arm or make some other intimate but totally benign gesture.

BE CONFIDENT (but not intimidating)

What lies behind us and what lies before us are tiny matters compared to what
lies with in us. - Emerson

hahaha! Actually joked with a friend about the need to get him drunk. Unfortunately, the one time we drank together was early on and I think both of us were still on our best behavior.

There is flirting, for sure. I have actually stayed at his house and he fixes me coffee (and remembers how I like it) and breakfast in the morning, makes sure I am comfortable and have a sweatshirt, towel, etc and finds excuses for me to stay longer than I need to. He also asks me repeatedly where I want to sleep (there are several options) and I suppose he could be fishing in a way to see if I choose his room, but that seems like a big leap given the current state of things. So he is either interested or is the greatest host ever. There is also some text flirting going on, although most of our interactions are face to face or on the phone.

Physically, there hasn't been anything that couldn't be considered platonic, although I noticed that once we started sort of flirting with each other, he all of a sudden became very concerned with helping me while hiking, such as turning around and offering a hand (which I almost always take, even if I don't need it), and he never did that before. I tried the casual "touch his arm while talking" move, but it didn't lead anywhere. I figured it was dead in the water at that point, but then he called me to tell me he wanted to spend time together. Like I said, I've never been one to read too much into things, so this is kind of new. I think I'm probably not reading enough into it, if anything, my radar is generally off and I've been told in the past by guys that they were trying to give me "the signal" and I've been oblivious. I don't want to make a fool of myself, but that might be a necessary evil to get to the bottom of "does he or doesn't he" at this point, I guess.

He is crashing at my house this weekend before an early hike, so maybe I need to turn up the heat a bit, because I really feel like I accidentally give off the "not interested" vibe out of nervousness. Besides the physical tension on my part, we get along very well, talk about everything, his dog loves me, and it's super comfortable.

And I'm okay if we just stay friends, but with the flirting and the vibe I'm getting, I think there's more there, so I would kind of like to figure it out either way before much longer. My friend/his step-sis is all for it and supportive, though I don't share any of this with her because I don't want to put her in the middle.

He might very well think you just want to be friends and he doesn't want to scare you off.

I like the sit on the couch and watch a movie suggestion and the "take his hand" suggestion. Sit close to him on the couch and, at some point, just take his hand and see what happens. It does imply something romantic, but it's not super aggressive or overtly sexual.